Transient imine as a directing group for the Pd-catalyzed anomeric C(sp3)-H arylation of 3-aminosugars

Juba Ghouilem; Sokna Bazzi; Nicolas Grimblat; Pascal Retailleau; Vincent Gandon; Samir Messaoudi

doi:10.1039/d3cc00046j

Transient imine as a directing group for the Pd-catalyzed anomeric C(sp³)-H arylation of 3-aminosugars

Juba Ghouilem
, Sokna Bazzi
, Nicolas Grimblat
, Pascal Retailleau
, Vincent Gandon
, Samir Messaoudi

Research output: Contribution to journal › Article › peer-review

Abstract

The first example of Pd(ii)-catalyzed anomeric arylation of 3-aminosugars is reported by using an L,X-type transient directing group (TDG) approach combined with an external 2-pyridone ligand. The released free amine was in situ transformed into an azide function, which was then exploited in a CuAAC to increase the molecular complexity and prepare a variety of complex substituted C3-triazolo C-glycosides in good yields.

Original language	English
Pages (from-to)	2497-2500
Number of pages	4
Journal	Chemical Communications
Volume	59
Issue number	17
DOIs	https://doi.org/10.1039/d3cc00046j
Publication status	Published - 31 Jan 2023
Externally published	Yes

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10.1039/d3cc00046j

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title = "Transient imine as a directing group for the Pd-catalyzed anomeric C(sp3)-H arylation of 3-aminosugars",

abstract = "The first example of Pd(ii)-catalyzed anomeric arylation of 3-aminosugars is reported by using an L,X-type transient directing group (TDG) approach combined with an external 2-pyridone ligand. The released free amine was in situ transformed into an azide function, which was then exploited in a CuAAC to increase the molecular complexity and prepare a variety of complex substituted C3-triazolo C-glycosides in good yields.",

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AU - Ghouilem, Juba

AU - Bazzi, Sokna

AU - Grimblat, Nicolas

AU - Retailleau, Pascal

AU - Gandon, Vincent

AU - Messaoudi, Samir

PY - 2023/1/31

Y1 - 2023/1/31

N2 - The first example of Pd(ii)-catalyzed anomeric arylation of 3-aminosugars is reported by using an L,X-type transient directing group (TDG) approach combined with an external 2-pyridone ligand. The released free amine was in situ transformed into an azide function, which was then exploited in a CuAAC to increase the molecular complexity and prepare a variety of complex substituted C3-triazolo C-glycosides in good yields.

AB - The first example of Pd(ii)-catalyzed anomeric arylation of 3-aminosugars is reported by using an L,X-type transient directing group (TDG) approach combined with an external 2-pyridone ligand. The released free amine was in situ transformed into an azide function, which was then exploited in a CuAAC to increase the molecular complexity and prepare a variety of complex substituted C3-triazolo C-glycosides in good yields.

U2 - 10.1039/d3cc00046j

DO - 10.1039/d3cc00046j

M3 - Article

C2 - 36752765

AN - SCOPUS:85148437732

SN - 1359-7345

VL - 59

SP - 2497

EP - 2500

JO - Chemical Communications

JF - Chemical Communications

IS - 17

ER -

Transient imine as a directing group for the Pd-catalyzed anomeric C(sp3)-H arylation of 3-aminosugars

Abstract

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Transient imine as a directing group for the Pd-catalyzed anomeric C(sp³)-H arylation of 3-aminosugars